Diamond Head Homes with Canal View

Welcome to Diamond Head, a breathtaking gem nestled on the southeastern shore of Oahu, Hawaii. This iconic neighborhood is renowned not only for its stunning landscapes but also for its vibrant culture and rich history. Dominated by the majestic Diamond Head Crater, the area presents a unique blend of natural beauty and urban convenience. Residents enjoy easy access to pristine beaches, lush hiking trails, and a plethora of dining and shopping options, making it a sought-after destination for both locals and visitors alike.

One of the most alluring features of Diamond Head is the availability of homes with picturesque canal views. Imagine waking up to the gentle sound of water lapping against the shore, with the sun rising over the tranquil canals that weave through this enchanting community. These homes offer a perfect blend of serenity and sophistication, providing an idyllic setting for relaxation and entertainment. Whether you’re sipping your morning coffee on the lanai or hosting a sunset gathering with friends, the captivating views create an atmosphere of peace and luxury.

In addition to the stunning scenery, living in Diamond Head means being part of a vibrant community. The area is home to a diverse population, with activities and events that cater to all ages. From farmers' markets to local art festivals, there’s always something happening just around the corner.

If you’re seeking a slice of paradise with the charm of canal-side living, Diamond Head is the perfect place to call home. Experience the allure of this extraordinary region, where every day feels like a vacation!

Newest Diamond Head Homes with Canal View

$13,800,000

5 Beds ⋅ 7 Baths ⋅ 202611456 MLS ⋅ FS - Fee Simple Tenure

The Paiko Retreat stands as a true Architectural Masterpiece after a comprehensive restoration. Sitting on over an acre of mature landscaping, Kanewai Spring, waterfalls, and koi ponds, there’s no place quite like this home. A unique estate designed by John Hara in 1983, Hara brings an intentional, open-air feeling to this home like he built at the Honolulu Museum of Art, UH West Oahu, and Punahou School. Spanning 9,295 square feet, the interior is vast, yet warm and deliberate. A dedicated primary wing and private sitting room tucked away from the main entertaining areas, plus four guest bedrooms, each with its own ensuite bath and connected by a custom glass elevator. A media room, family room, and private offices provide space for everyone. The transition to the sweeping lanais is seamless. The grounds carry the calm of a private Japanese resort, with gardens and water features weaving through the property. You have direct frontage on Kanewai Spring feeding into Historic Paiko Lagoon. Because it’s a state wildlife sanctuary, the view is strictly nature—quiet and serene. Evenings here are best spent on the lanai watching shorebirds wade through the shallow waters.

6015 Kalanianaole Highway, Honolulu

Listing courtesy of Compass.

$10,500,000

5 Beds ⋅ 7 Baths ⋅ 202608794 MLS ⋅ FS - Fee Simple Tenure

Introducing a rare new luxury construction in the heart of Kahala, where no detail has been overlooked. This stunning estate features a primary residence and guest cottage/gym, both crafted with the finest materials, including custom cedar ceilings, copper gutters, high-quality composite roofing, and lava rock accents throughout. Designed for the discerning buyer, the property boasts a resort-style pool, whirlpool, koi pond, custom cedar gazebo, and expansive lava tile patios and walkways. Inside, you will find a marble primary bath tub, custom wood ceilings, lava tile feature walls, acoustic wall paneling, vanities, and interior tiling of the highest caliber. A true one-of-a-kind opportunity to own a brand new, thoughtfully designed luxury home.

4561 Aukai Avenue, Honolulu

Listing courtesy of Compass.

$4,800,000

5 Beds ⋅ 7 Baths ⋅ 202528272 MLS ⋅ FS - Fee Simple Tenure

Perched on the eastern facing perimeter of the prestigious Hawai’i Loa Ridge, 875 Ikena Circle brings a unique grandness to Oahu. Enjoy picturesque views of the Pacific Ocean, Hawai’i Kai Marina, Koko Head, and Portlock. A multi level layout provides the ideal recipe for entertainment and multigenerational living. The main level of the home showcases vaulted ceilings and an abundance of natural light. A spacious primary bedroom suite is situated on the main level adjacent to the living room. Make your way downstairs where you are presented with 3 suites along with an additional living room that opens to the pool deck. A detached pool house provides a personal sanctuary that can be utilized as a home office, a space for guests, or a cozy man cave. Amenities within the community include: Gated entry, 24/7 security, tennis & pickleball.

875 Ikena Circle, Honolulu

Listing courtesy of Coldwell Banker Island Prop.

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.